Reaction #4017

Reaction equation

2-chloro-1,1,1-triethoxyethane

2-aminothiophenol

→

2-chloromethylbenzothiazole

Yield 91.3%

Solvents

methylene chloride

Conditions

Workup

1. 1
   Washthe resulting solution was washed with 3N HCl (10 ml)
2. 2
   OtherThe organic portion was evaporated
3. 3
   Otherthe residue chromatographed over silica gel

Procedure

A solution of 2-chloro-1,1,1-triethoxyethane (5.9 g) and 2-aminothiophenol (2.5 g) was heated at 80° C. for 15 minutes. After cooling to room temperature, it was dissovled in methylene chloride (30 ml) and the resulting solution was washed with 3N HCl (10 ml) and then with water (20 ml). The organic portion was evaporated and the residue chromatographed over silica gel to obtain 2-chloromethylbenzothiazole (3.35 g; 90% yield), m.p. 34° C.

Source